We Welcome Your Application to Join Us!

We build each of our groups with care, keeping the groups small (no more than twelve students), and paying close attention to age, grade, gender, and the mix of hometowns and schools. Our goal is to put together great groups — groups where nice kids thrive in a supportive, wholesome, and caring environment. Please note: availability as shown is based on students traveling without a friend; if your child is interested in traveling with a friend, please call our office for availability.

Important Information about Availability


This departure of this trip has good availability. Apply as soon as possible since availability changes quickly.


This departure of this trip has limited availability. Apply as soon as possible, and on receipt of your application, if space is still available, we’ll confirm a spot for you. If all of the spots are taken, we’ll call you to discuss options.


This departure of this trip is currently full — please call us to discuss options.

How to Apply

Apply online using a credit card for the $795 deposit (your card will not be charged until we confirm a spot for you). Applications are reviewed in the order in which they are received (we do not hold spots over the phone).

When to Apply

The flow of applications starts in July and peaks in January/February. Some groups fill by the December holidays, and others will have space into the late spring. Our advice? Apply as soon as possible — it only takes a few minutes — and we’ll get to work right away to find a great spot for you.


Call (413.458.9672) or email (info@overlandsummers.com). We look forward to hearing from you.

Looking Ahead: 2021 Perspectives from Leader Hiring

Teamwork & Leadership

Leaders on an Overland Trip

Overland’s founder and director, Tom Costley, recently chatted with Beth Larcom and Luke Costley, the Overland leader hiring team, to discuss their efforts for summer 2021. Read our current COVID-19 policy here.

Tom Costley: Tell me a bit about your goals for leader hiring this year.

Beth Larcom: Our goal for this year, simply put, is to put together an incredible staff. We want to find the most fun, capable, and caring leaders to join our team – we want to find and work alongside folks who will give 110% effort to every single thing they do. More than that, as a leader hiring duo, we want to be a helpful and supportive team that our leaders trust and rely on from the first time we speak to an applicant, all the way through to the end of their summer of leading.

Tom Costley: What does leader recruitment look like?

Luke Costley: We feel incredibly fortunate to have such a strong network of Overland leaders and families. We also want to work especially hard this year to find leaders from new communities, and in doing so, broaden the Overland network. We spent the first part of our year getting in touch with leaders who have led for us in the past and dialing in our systems for virtual recruiting. As we dive into the heart of hiring season, we’re eager to create new partnerships at schools around the country and build those relationships.

Luke and Tom Costley
Luke and Tom enjoying a perfect summer day

Tom Costley: Does the pandemic offer any silver linings in terms of recruitment?

Beth Larcom: The pandemic definitely gives us more time to think critically about, and reflect on, our processes in hiring. In a normal year, we would be travelling all around the country to visit schools and set up in-person interviews, which is of course fun and exciting, but it does take up a lot of time. Because we’re sticking to our home base in Williamstown, every ounce of our effort is going into figuring out how we can find the best staff possible (and making that happen!).

Tom Costley: Are there certain qualities you’re looking for in prospective leaders?

Luke Costley: We appreciate how there is no single style of leadership that works at Overland. We like to say that leaders should be themselves and let that genuine spirit resonate with their groups. There are certain commonalities though that we see across the board: our leaders are wholly committed to the work of building relationships with and among their group members and their co-leaders.

Tom Costley: Do you have any advice for prospective leaders?

Beth Larcom: Distinguish yourself as a leader. We look for overachievers – people who do a lot, and excel at all they do. Show us what you’ve got!

Beth Larcom from Leader Hiring
Beth out on a hike. In 2019, Beth led our Pacific Coast trip

Tom Costley: Anything else to add?

Luke Costley: Our conversations with returning and prospective leaders brighten our days. It’s a joy to hear from these folks — they’re engaging, and interested in the world, and caring for those around them. It comes through over the phone, over Zoom calls, over emails and updates. All of which is to say, we can’t wait for the summer! It’s going to be an absolute blast.

Tom Costley is Overland’s founder and director. After a first trip to the Alps, Tom fell in love with the simple grandeur of Switzerland’s alpine passes. Tom, his wife Liz, and their children take family trips to the Alps every year. In the office, we like to debate which of the world’s mountain ranges are the most beautiful– the Costleys say the Alps win every time.

Tom and Liz wear their Overland shirts as they enjoy the Alps in August

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